Trials and Tribulations of Dating in the Modern Age

October 5, 2017

We all compile funny and embarrassing stories over the course of our lives. Like that time you slipped and fell in front of the cutest boy at school and he laughed at you. Now that’s just an example I pulled off the top of my head. It absolutely never ever happened to me. No way. No how.

Now, I’m definitely not a subject matter expert in funny and embarrassing stories…. Scratch that, I’m pretty sure I wrote the handbook on how to be awkward and end up embarrassing yourself. Today’s story isn’t really embarrassing, well at least not for me anyway. Today I thought I’d reach into the vault and pull out an old first date story from way back when I lived in Seattle. I remember the ladies at the office used to love when I’d come in with these horrifying first date stories. Like the time my date asked our server for her number right in front of me…. Yeah, he was a winner. Or the time my date “forgot” his wallet. Anyway, this one is a gem. I hope you enjoy it and I hope it makes you laugh. If you do like it I might be persuaded to throw in some more recent stories. I have a couple doozies.

The Fireman – Seattle WA – c. 2008

The best stories of my life begin with, so I had a date last night; not because of the intensely high quality of them, believe me, but because of their pure comedic value. Let me pull out an oldie but goodie for you….

Back when I lived in Seattle it was quite difficult to date. In the land of Microsoft and Amazon to say that people were, in general, socially inept and mostly introverted would be the understatement of the century. Here I go already, offending the greater population of Seattle, but hey, this is my story right? Don’t get me wrong, Seattle is an amazing city and I’d happily live there again in a heartbeat but I think Seattle is mainly a city of introverts who on rainy days sit in their comfy bay windows curled up in blankets sipping coffee and reading books. Really a lovely way of life but it doesn’t really bode well for being social and certainly not for dating.

Ok, so back to my story? Well, in this day and age you’ve heard of online dating I’m sure and in Seattle it is alive and well as most people there do choose to type conversations out rather than speak them. There I go offending again. Anyway, I had been chatting to this fireman and we decided to meet up one night at this little local wine bar in Belltown. I was excited; I mean, come on, fireman, need I say more?

I showed up to the wine bar and now I know I have a distorted and utterly low self-image, however, this guy who claimed to be six feet tall couldn’t possibly have been more than an inch or two taller than me and I’m pretty sure he might have even weighed less than me. Really? This tiny little man was a fireman? Ok, let’s go with it but let me also mention a few other things. This was a date in the evening and at a wine bar. I’m sure I had my standard uniform of jeans, heels, black top, a couple pieces of jewelry and minimal makeup. Back then I was the queen of the messy bun, so I imagine that made an appearance as well. So yes, I agree, I wasn’t a show stopper but I would like to think that I was at least put together.

Now this fireman, whose name I really can’t remember anymore, shows up in shorts for an evening date with black sneakers, white socks and a yellow polo shirt with a couple of black stripes across the chest. Now come on, picture this with me. I rock up, mostly put together and very presentable and likely slightly nervous to see this guy standing there dressed in black shorts, black sneakers and a yellow polo shirt with a black stripe. Did I mention the white socks? He’s standing there, hands in his pockets, staring up into space, rocking back and forth toe to heel without a care in the world like he’s there to meet absolutely no one but is just rocking the day away to his own little tune in his head.

I admit it, the first thought that popped into my head was “Charlie Brown. I’m going on a date with Charlie Brown. Someone save me now.” The second thought was of course, this is going to be the funniest story ever.

So I walk up to Charlie Brown to say hello and get this night started. I think I got a head nod. Not even a hello, nice to meet you. Hands still in pockets, no handshake, no peck on the cheek hello, because well this is Seattle and contact of any kind is a major commitment. And yes, I am joking and really just blowing the Seattle thing out of proportion for the benefit of my story.

We walk in, Charlie Brown and I, and we sit down at a lovely little table by windows that are thrown wide open and order a glass of wine each. Now it’s early evening in Seattle summer and we have many hours of daylight left so at the minimum I’ll be able to watch the people of Seattle wander by. The weather is warm. The air is fresh and there’s a nice breeze wafting in. This is pretty much the only comfortable part of my evening.

The conversation was at best dull. Much to my relief Charlie Brown all but chugged his glass of wine. There was no mention of ordering food or even a tiny little cheese plate. I remember thinking, oh thank God; he thinks this is going as horribly as I do and I’ll be out of here and in my pj’s well before 8pm. Yeah, I jinxed myself with that thought. With his big saucer eyes and childlike features he looks up at me and Charlie Brown actually says, “let’s get a bottle” and proceeds to flag the next server down to order it. Now mind you, I haven’t even finished half my glass of wine and all of sudden we have a bottle arriving. Again, no mention of food and yes, in retrospect I should have just ordered something but perhaps I was in a state of shock.

While the conversation was still at a minimum, it allowed more time for wine drinking and Charlie Brown managed to finish half the bottle before I finished my first glass. Probably a good thing for me to keep my wits about me. The more he drank the rosier his cheeks got and the more he drank the more downhill the already abysmal conversation went.

By the end of the bottle, which disappeared quite quickly, I was able to say, “Thank you for a lovely evening but I really must get going as I have an early morning tomorrow”. I had practiced the line in my head for about thirty minutes before the bottle was actually finished, you know, due to lack of conversation. I was relieved I could go ahead and cut the night short.

Well Charlie Brown had other ideas and insisted on at least walking me towards my building under the guise of being a stand up gentleman making sure I got home safely. When we got to my high-rise, his hands went back into his pockets and his rocking resumed but this time looking at me with his rosy drunken cheeks and big saucer eyes, he actually had the audacity to say, “This has been a really good night and I sure would like to come in and spend the night”. Now I’m not sure if the next bit actually happened out loud or not but there was definitely maniacal laughing going on in my head. I was in absolute hysterics. Were he and I actually even on the same date? And did he seriously think there was a chance in hell he was getting anywhere near my apartment? I’m sure if he were sober he would have noticed the look of shock and horror on my face. Wouldn’t he?

I’m sure this is needless to say, but I declined his underwhelming offer for a roll in the sack, entered my building alone, laughed the entire way up in the elevator, unlocked my door and promptly called a girlfriend to say “you won’t believe this shit; I couldn’t make it up if I tried”. And that my friends, is today’s story that, like the date, I will keep short though I might add, if it wasn’t obvious already, there was no second date for me and Charlie Brown.